The First Synthesis of disaccharide a-iminosugar
Date Issued
2015
Date
2015
Author(s)
Jiang, Cai-Rong
Abstract
Due to the increasing drug resistance, design and synthesis of potent antibiotics is urgent and critical to scientist. Bacterial TGase is considered as a potential target due to the lack of the eukaryotic counterpart, easy access and no resistance to current drugs. In order to design new antibiotics against TGase, the detail study in protein-substrate interaction and the establishment of TGase assay are required. However, preparation of the key component, TGase substrate-lipid II, is difficult due to the low natural abundance and complex structure. Researchers have developed various lipid II, most of which are based on glucose analogues. In this thesis, we are focus on the designing of new lipid II based on iminosugar analogues. According to the good resistance of the iminosugar analogues and the similarly structure of the glycosylation transition state , we can apply these compound to the study of lipid II. However, the synthesis study of the α-C-iminosugar is few and difficult. We have designed a series of steps, wittig reaction, Swern oxidation, reductive amiation and hydroamination, to afford the ideal iminosugar target.
Subjects
iminosugar
Type
thesis